11 comments/ 130736 views/ 20 favorites Virginity Has Its Perks Ch. 01 By: Bobby_3111 This is a work of fiction. Sometimes I wonder if life gets easier. My Mom, Jeanne, used to tell me that "Every experience is just a part of growing up Bobby". Well if it was then it was literally hell growing up. At least for me it was (computers, debate team, etc, you get the idea, half nerd, half normal guy, still an outcast), my sister Holly on the other hand seemed to have it easy. She graduated 2 years ago and got a scholarship to one of the local community colleges (she still stays at home in her old room to save money). So here I am sitting in my room staring at my computer screen wondering just what the hell was I going to do tonight. It's been exactly one week since I had graduated high school and so far all I had managed to do for this summer so far was sit in my room and play games and watch TV. The big plan was to start searching for a summer job and make a little money before classes started next fall for community college. I would do the same as sis and stay at home for my first 2 years then if I got accepted to a 4 year school would see what my options were. It's not that I didn't have friends, I did, I was just depressed for another reason. I am still a virgin. Yup, while some guys get laid early on in life I was one of the lesser' on the social scale. I'm one of the nervous fidgety types that get tongue tied and feel my stomach tie up in knots when it comes to asking women out on a date. I've reasoned it out a thousand times and I still can't seem to get a grip on things when it comes to women. And for that reason I am a virgin. It's not that I can't talk to women; I can, just when it comes to the asking out part my fear of rejection overrides my hormones. And I know I'm not a bad looking guy, I started lifting weights every day this past year and do cardio at the gym every other day, sometimes the bike, sometimes the treadmill, I keep myself in shape. At 5'10", 180 lbs with brown hair and blue eyes I'd say I look pretty good for an 18 year old. My mom tells me I got my dad's good looks and that's about the only thing of his I take after. Oh well, I still got internet porn and hand lotion, someday I'll get over my fear, just takes time I guess. Glancing at the clock on the bedside table it was 4 pm, mom should be home soon and my sister Holly wouldn't be too long behind her. Guess jerking off will have to wait till later tonight. Might as well head downstairs and see whats on TV. Flipping through the channels sitting there in my sweat pants and t-shirt I hear a car pull up in the driveway and into the garage. After a couple minutes I hear a key in the lock and my mom opens the door and walks in. Now some people just look at their mother as their mother, they never really notice how attractive or unattractive they are. My mother Jeanne was attractive; I first noticed how she looked when I hit puberty. At 5'6" she couldn't have been more than 115 lbs, with the stylish short brunette hair and blue eyes she had a stare that could pin you to the wall (I know, when I got in trouble in my younger days she always used it). And she had the most perfect set of big tits I had ever seen on a woman, I don't know the size, but if I were to guess I would have to say in 36+DD range. Overall she was a knockout, even if she didn't like to flaunt it very often. Mom was a very successful real estate agent; she could sell almost anything if it was planted into the ground. Right before I was born our dad had run out on us, mom said he had given the excuse he just couldn't be a family man and left one night. Mom said she had never heard from him again, good riddance I thought. After I was born mom had already finished high school so she decided to get a job as a secretary to one of the real estate firms in the nearby city. She worked there for 3 years learning all about the business and finally became a real estate agent herself. She opened her own agency after 5 years of being in the business and now after only 10 years she had a well earned reputation and a very comfortable living for herself and us. Today she had on the light blue silk blouse with navy blue skirt, with high heels. A conservative look to be sure but it still didn't hide the fact she had something up top that made men drool after her. Noticing me on the couch "Hi Honey, how was your day?" she says while leaning to kiss me on the forehead. "Just another day" I replied sighing. Hoping she would leave it at that I start flipping through the channels again. Of course, she didn't. "Bobby whats wrong?" she asks while sitting next to me and looking at me with that concerned mother look. "Mom its nothing, it's just guy stuff, don't worry about it" I replied. "Guy stuff huh? Is it about girls?" she asked. With my face reddening a bit I keep my mouth shut hoping she'll take the hint and not embarrass me any further. "Honey talk to me please?" she says while stroking my hair like she used to when I was little. Why can't I ever just keep my mouth shut or tell a really good lie every now and then I wonder. "Yes if you must know it's about girls." I said flipping through the channels. She looked at me for a few seconds then took the remote out of my hand and turned off the TV. "Look at me Bobby." She said. It was the same voice she used when she wanted my attention and it was damned hard to ignore, so I didn't. I turned and looked at her and she just smiled still stroking my hair and asked me "Now whats the problem sweetie?" For some strange reason my mom sitting there looking at me so concerned and understanding like and smoothing my hair back had a type of hypnotic effect on me. And all at once I just blurted out "Mom I'm a virgin!" Now with my face as red as some of the wine she had in the fridge I buried my face in my hands and just sat there. Her hand had stopped and moved to my shoulder, I felt her give me a gentle squeeze. "Honey look at me." She said. I looked up and she was still smiling. "It happens for everyone at some point in their life, for some it takes longer than others, it's nothing to get upset about." She said soothingly. "Yea I guess." I reply looking back at the TV. "Have you been on any dates lately?" She asked. I guess one thing I should come clean about. Every now and then just to keep up an illusion of a normal teenage boy I would on occasion borrow the car on a Friday or Saturday and go out of town on the pretense of having a date. I get the suspicion my sister knew I wasn't going on a date, but I'm pretty sure I fooled my mom into believing it. And now I'm pretty much fucked I thought. Sighing to myself I decided to tell mom the truth. "Mom I've never been on a date before" I said still looking at a blank TV screen. I glance over at my mother and see the shocked look on her face, just sitting there looking at me in disbelief. "It's true, all those times you loaned me the car I drove over to the mall or across town to the movies or the bookstores and just hung out there, sometimes with friends and sometimes by myself." I said. Glad to finally get it off my chest. "Honey why haven't you told me of this before?" The concerned mother was back again. "Look mom it's not that I don't want to date, I just can't. When I try to get up the nerve to ask a girl out my insides knot up and I can't think straight. I'm so afraid I'll be rejected that I just can't do it." I say looking up at her. Just then we hear my sister's car pull up in the garage. Patting my leg mom gets up and moves to the hallway, just before she leaves the room she turns back to me. "We're going to talk about this later Bobby, ok?" "Ok Mom." Saying that she turned and went upstairs. Hearing her bedroom door shut I turn back to the TV and turn it on to see if I could find something to watch. Less than a minute later my sister walks in the door carrying a couple bags from one of the local bookstores. Now my sister Holly isn't a mirror image of her mother, she is about the same height and has close to the same cup size of mom (somewhat smaller, but not by much) and that's where the comparison ends. Where mom's hair is dark, Holly is a natural red head, with freckles to match. Mom's hair is cut short and Holly's is below shoulder length. When she has it in a braid it looks like a trail of fire swaying down her back. Today she had it in a simple pony-tail and wearing jeans and a white t-shirt. "Hey lil bro wanna help me out here?" "What for? Looks like you got it handled." I said grinning. "Bah, I still got some stuff in the car I gotta bring in, my pack and a couple of charts I've been working on for a project, will you run out and grab them for me?" She said practically begging. Sighing I turn off the TV, nothing good on anyway. "Ok but you owe me." In response she stuck her tongue out at me. Going to the door I moved around her as she was headed for the stairs and noticed her jeans had slipped a bit on the backside. I saw a sight that caused me to stop dead in my tracks; she was wearing a black silk g-string. That in itself would mean little, but with the faded jeans slipped down as they were and her tanned skin it made it impossible for me not to stare. And apparently my cock had the same idea; it started rising up to see what the fuss was about. Watching her ass sway back and forth while she crossed the room with that thin piece of silk swishing ever so delicately across her skin was hypnotic to say the least. "Enjoying the view?" I heard a voice ask. Startled I looked up and saw my sister looking over her shoulder at me from the bottom of the stairs with a wicked little grin on her face. Knowing I had been caught all the blood left my cock and went straight to my face and I made a hasty exit out the front door. Opening the door to her blue compact I reached inside and grabbed her back pack and a couple of long rolled up charts she wanted and pulled them out. Breathing heavily I decided to stay outside a few minutes and let myself calm down before going back in. After a couple minutes I looked into the driver's side mirror and saw that now there was a reasonably normal color to my face I went back inside lugging my sister's stuff. When I came back inside my sister must have gone on upstairs so I unceremoniously dumped all her stuff at the foot of the stairs and went back in the living room to try to watch TV this time. A few minutes later I heard my mom calling for me so I turned off the set and went upstairs to her room. Knocking on her door I heard her voice say come in and I opened the door and went inside. My sister was sitting there on the edge of the bed still in her jeans and t-shirt. She smiled when she saw me and winked. I decided to ignore her and looked to mom. Mom had changed into an old t-shirt and a pair of tan colored shorts. She asked me to run pick up some of her suits from the dry cleaners across town and to stop at the Chinese place on the way back, as she didn't feel like cooking tonight. "Sure mom. Need anything else?" "Nah sweetie that's all." She said smiling. She gave me the keys and as I was about to leave I noticed my sister still grinning and she suddenly giggled. I turned to look at her and then I noticed mom now grinning at me, confused I shrug my shoulders and left the room, leaving the door open. The trip across town took more than an hour, mainly because of the afternoon rush of people wanting to get home. But other than that it was uneventful, I got the dry-cleaning mom wanted then on the way back stopped by the Chinese place for takeout. With the food and suits now in the car I headed for home. More than halfway back I had to turn on the headlights, it was getting dark. It was close to 6 pm by the time I pulled into the driveway and pulled into the garage. I unloaded the car and brought the takeout and set it on the kitchen table then took mom's dry-cleaning upstairs to her bedroom. I heard the shower on and figured she must have just jumped in so I opened the door and walked in. What I saw stopped me dead in my tracks. There was mom with her back to me, looking through her closet with not a stitch of clothing on. Her ass was nothing short of perfect, very light tan and perky as they come, and her legs, they looked as smooth as silk, just in that glimpse my cock shot up to half-mast in a split second. Time seemed to stop for just a few seconds, or maybe it was my lust addled brain that made it seem that way. But all too quickly time started again and my mother must have sensed me in the room or felt some cool air rush in from the door opening, because she looked over her shoulder and just winked at me. She then looked back to the closet and calmly pulled a cream colored robe out and put it on with her back still to me, then turned to face me as she was tying the sash. "Well?" Mom asked Suddenly realizing just what I was doing, I looked up at her face and saw her grinning and for some reason I felt embarrassed, but not mortified like I should. Instead of hauling ass out of there I just grinned sheepishly and lay her dry-cleaning down on the bed and made a retreat out the door without looking in her direction again. Just as I was about to shut the door mom told me to wait a sec. "Honey?" she said, trying to get my attention. She had to have had her robe on by now I reasoned. So I cracked the door and stuck my head in. She was brushing some lint off her robe or something when I stuck my head back in. "Whats up mom?" I asked "Take this and throw it in the laundry room for me sweetie." I opened the door a little further and stepped halfway into the room and looked around, I didn't any clothes anywhere except for the dry-cleaning I had just brought in. Then I noticed she was undoing the sash at her waist and then slowly, while looking me straight in the eye, she opened it and shrugged her shoulders. It fell into a pool at her feet. I was stunned, I started breathing hard and my cock started rising of its own and this time I took no notice of it. I just couldn't take my eyes off of her, she was drop dead gorgeous. I looked her up and down, from the tops of her big tits with huge nipples down to her perfectly shaved pussy lips, I was mesmerized by her beauty. Then I was suddenly jolted back to reality when she reached down and handed me the robe, still grinning she shooed me out the door as if she wasn't standing there naked and shut it behind me. I stood there for a moment to get my breathing under control and looked down. To my horror my cock was standing at fullmast. Mom had to have seen that I thought. I was never one to brag but I did have a nice tool, a little over 8 inches would be a good estimate. Ok calm down Bobby, even if she did see it think for a minute, I thought. She wanted me to see her, that's why she pulled her robe off, to get this kind of reaction from me. But why would she do that? I argued with myself for a minute or so before my cock had finally deflated enough to be hidden in my sweats again. Composing myself I went downstairs to the laundry room and tossed her robe over in the hamper by the wall, then went back into the kitchen to get out some of the food that I had brought home. Holly came down a few minutes later just as I was setting into some honey chicken. She had changed into a pair of running shorts and a blue wife beater. Coming up to the table she took out a few things and made herself a plate. For some reason after she sat down she stared at me, as if she wanted me to make conversation with her. After I was almost finished eating I finally took the bait. "What?" I asked. "Hmm?" she replied smiling around a mouthful of beef teriyaki. "What's with the staring and grinning?" "Why I don't know you mean Bobby" she said playing innocent. "Fine be ignorant then." I said finishing the last of my food in annoyance. She just kept smiling as I got up and rinsed my plate off and set it in the drain to dry. Just then as I was about to leave the kitchen my mother walked in, she had on this light cream colored kimono style robe, and was still drying her hair with a towel. "Smells good" She said as she went to get a plate from the cabinet. Seeing no reason to hang around in there I decided to head up to my room to play some games a bit and maybe get a chance to take care of my frustration. Just as I was about to leave Mom called to me. "What's up mom?" I asked turning around. "We need to talk sweetie about your problem, it might as well be now." "Holly is here Mom ..." "Yes I told her about it." "Mom!" I said I couldn't believe my ears, she had told Holly?!?! "It's ok Bobby, it's no big deal, and mom told me so she could get some advice since I had been dating more recently than she has." Holly said with a small smile. For some reason Holly's smile wasn't one of the smirks I was accustomed to, this time she actually seemed like she wasn't teasing, women are strange I thought. Mom was speaking again, it took me a moment to get over my shock and hear what she was saying. "Bobby you have to get over this fear you have, you can't have a normal life until you do." The concerned mother was back and this time Holly took on the same look as well. I went back in and sat back down, not saying anything just staring at the table. After taking a couple bites of her food Mom got up and got a bottle of wine out of the fridge and opened it and told Holly to get 3 glasses out of the cabinet. "I think we all need to relax a bit if we're going to talk about this Bobby." She said. After pouring us all some wine Holly sat back down and sipped hers as did mom, but as for me I rarely get the chance to drink so I downed mine in 2 gulps, mainly from all the embarrassment I had had today. "Slow down Bobby, you need to relax sweetie, not get drunk." Mom said, while pouring more into my glass. "Sip it sweetie" she said setting the bottle back down. So I did, and then the inquisition started. Mom and Holly both wanted details as to what exactly happens when I try to talk girls, and as best I could I explained. They wanted to know what I had been doing to try to get over this fear and all the ways it sets it off, etc. This went on for a little while, and somewhere during the conversation we finished off the first bottle and started on a second one. During a lull in the conversation Mom glanced at the clock and saw it was well past 9 pm, and said we should continue in the living room where we would be more comfortable. Grabbing a third bottle out of the fridge we all went into the living room where mom and Holly sat on the couch and I sat on the love seat. But mom wasn't having it, she told me to get in between her and Holly on the couch so we could talk. Holly just giggled; she was pretty lit by now. As for myself I was halfway to being drunk myself and didn't think anything of doing what my mother told me so I moved over to the couch and sat in between them. "Alright, we've discussed all the ways you've tried to get over this and all the ways you haven't, but I think it's time to try something new." Mom said with a wicked little grin. Holly knowing that to be her cue stood up and pulled her wife beater over her head. Her tits sprang out into the open air and bounced a bit before settling back down, she casually tossed the shirt to the side and grinned at me. I just stared with my mouth open like an idiot, not talking or even blinking, they were just gorgeous. Her tits were almost as big as mom's with big nipples to match. My cock instantly rose up to full mast and was pushing at the waistband of my shorts. Holly sat down on the loveseat and crossed her legs and just leaned back into the cushions, looking as if it were the most natural thing in the world to sit there with her top off in front of her mother and brother. Virginity Has Its Perks Ch. 01 I heard mom speaking again so I shook my head to clear it a bit and listened to what she was saying. "Now sweetie Holly and I spoke about this and you need to get over your fear of talking to women, so she's going to sit there and you're going to talk to her." "But Mom this is Holly, I talk to her all the time..." "I know sweetie, that's why she isn't wearing her shirt, with it off its almost as if she is someone different, doesn't she seem different sweetie?" Mom had a point, with Holly sitting there with her tits in plain view it was almost as if I didn't know her. "Yea mom she does." I said still staring at Holly's tits. "Ok mom, your turn." Holly said grinning. I felt mom move beside me and when I looked over she was standing up and undoing the sash on her robe. When the sash came off once again I saw the most perfect tits in my young life. Mom didn't have a bra on but she did have panties on this time to my dismay, the black lacy type. She let the robe pool to her feet and sat back down. Looking over at me she said "Now Bobby talk to me." At first I couldn't speak, I could only stare, in the short space of just 6 hours I had witnessed 2 pairs of real womanly breasts and seen a real shaved pussy for the first time. I snapped back to reality when I felt my mother's hand on my hair again, smoothing it back. She was whispering "Talk to me baby." I don't know why what happened next did, maybe it was her calling me baby, but instead of words coming out of my mouth when I opened it, I suddenly found my head nestled against her left breast and her nipple in my mouth sucking it gently. At first her hand stopped stroking my hair and tensed a little, but then it resuming its motion of going back down my head to my neck and rubbing back and forth gently. She started cooing to me softly and massaging my neck. As I suckled I felt more than heard my sister move up to us on mom's other side and she whispered "Mom, that's so beautiful" then I felt her on the other side and looked over seeing her take mom's right nipple into her mouth and sucking. Mom moaned then softly and with her right hand started running it through Holly's hair while looking down smiling at us. "This wasn't what I had in mind, but it feels so wonderful." She whispered, still moaning softly. I started to gently rub my left hand in circles on mom's belly and noticed my sister's hand slowly creeping up mom's thigh to her panties. Mom could feel it too apparently because she started to move her legs apart so Holly could get better access. Holly's hand was now gently rubbing mom's pussy through her panties as she started moaning louder. Not knowing where this was going or even thinking about anything I stopped my suckling for a moment and raised up and removed my shirt. Before I could resume nursing on mom's tit she looked over at me and gently pulled Holly off her and said "Sweetie look at your brother, he needs taking care of as well." She then stood up and pushed me back on the couch and then slowly slid her panties off, she then kneeled down and told holly to come closer. She guided holly's head to my chest where my sister sucked in one of my nipples, gently rubbing and biting. Mom then took the other and did the same, nibbling gently. I just closed my eyes and leaned my head back, enjoying the hell out of this. I now had 2 beautiful women sucking my nipples and driving me crazy, my cock was hard as steel sticking up in my sweats and getting so hard it was painful. Mom must have realized this because her hand drifted down and slowly reached inside and pulled it out of my sweats and slowly began to stroke it. With Holly still nibbling on my right nipple Mom suddenly stopped and I felt her move back, when I opened my eyes and looked down I saw her ever so slowly take my hard cock into her mouth and started to gently suck the head. At first I couldn't believe it, I was so shocked I didn't feel anything for a moment, then all at once the sensation of having my cock sucked for the very first time hit me. In the space of just a few seconds I couldn't hold on, the new sensation was just too intense, I erupted into her mouth and was cumming like crazy. I shot load after load and Mom never once stopped sucking, she swallowed it all. It was like a porn fantasy come true. And in my half-drunken stupor I suddenly realized that my mother had stopped sucking and was sitting there smiling at me and my sister at my side doing the same. "So Bobby, how do you feel?" Mom asked smiling still on her knees in front of me. "I feel fantastic mom" I said grinning like an idiot. Mom gently reached over and started stroking my semi-hard cock again and said "We need to get you hard again for what is next baby." "Lift up and Slide out a bit" Mom said sliding my sweats completely off me now. I obediently slid outward till my ass was on the edge of the couch. My sister, now totally naked standing on her knees next to me said "Open your mouth" and as I did as I was told Holly popped her left nipple into my mouth and told me to suck. And suck I did, as soon as I started Holly started moaning and rubbing her pussy and I knew she was getting worked up. While suckling my sister I felt my mother start fondling me and then I felt her mouth on my semi-hard cock again. With Holly holding my head with one hand and rubbing her pussy with the other she was soon cumming to a big climax as she yelped and moaned softly. It wasn't but a minute or so before my mother's intense sucking had me as hard as steel again and she told Holly to move back a bit to give her some room. At first I didn't know what she was doing, then suddenly she moved up on the couch and straddled me and in that split second I knew. I got nervous, excited, scared, I was a bundle of emotions all rolled into one. Mom smiling looked at me and said "Honey don't be nervous, this is a natural thing" I looked over at Holly and she was just smiling and reached over and stroked my hair to give me comfort. Mom looked down at me and asked "Are you ready sweetie?" I just looked up at her and nodded my head. Mom looked over at Holly and something passed between them because Holly got behind mom between my legs and I felt her hand on my cock moving it into place beneath my mother. Mom leaned down and whispered to me "Momma is going to fuck you now sweetie, your virginity is mine, and no one else's now." And with that she slammed her hips down on my cock taking me all in at one swift movement. Time stopped. It was indescribable; the wet blanket heat surrounding my cock was just insane. It was like a furnace it was so hot, but at the same time, it was welcoming, warm, loving, as if I was coming home. All at once time came back into focus and slowly ever so slowly mom was moving up and down on me, her pussy adjusting to my size after the first initial plunge. I felt Holly rubbing my balls as mom slid her hips up and down repeatedly, speeding up with each movement. "Do you like it baby? How does it feel not being a virgin anymore?" Mom asked smiling while riding my cock. "It feels fucking awesome mom!" I said panting. "You like when Momma fucks you don't you Baby? You like fucking that mommy pussy don't you? You like being back inside the place you came from? You like fucking the same hole you came out of so many years ago don't you baby?" Mom said panting fucking me like crazy; her hips were a solid blur going up and down. I felt Holly stop rubbing my balls and saw her move back onto the couch and she started kissing me, our tongues wrestling each other. I guess she felt left out because of the way mom and I were going at each other and decided to move next to me to get more involved. With Holly suddenly making out with me and mom's dirty talk and lightning hips I couldn't hold out anymore. I tried to draw back from Holly to say something but Holly grabbed my head and wouldn't turn loose. All at once I let loose, my cock started shooting load after deep inside my mother's pussy, and it must have triggered her orgasm because she started moaning like crazy and pinching her nipples. My sister noticed I was cumming and so was my mother, she released her tongue lock on my mouth and leaned over and took my mother's nipple into her mouth and started sucking her. Mom went crazy and start screaming. "That's it baby, cum inside your mother, cum deep in me, cum baby cum!" I did what was natural and pushed deeper into her by raising my hips up and gave her the last few shots as deep as I possibly could. She seemed to love it, thrashing around holding my sisters head to her tit. Moments later her orgasm seemed to have subsided and she released holly's head and collapsed on top of me, her head resting on my chest. Holly just sat there smiling and rubbing mom's back. "Mom that was the greatest thing anyone has ever done for me, thank you, and you too Holly" I said looking at them both. Holly just smiled and Mom raised her head up and grinned at me weakly and said "The night isn't over yet Bobby." At first I just stared at them, then I got the biggest grin on my face that I've had in years, tonight is gonna be one hell of a night! Virginity Has Its Perks Ch. 02 This is a work of fiction. Sometimes I wonder if life can get any better. Just the thought fills me with a humorous glow. It was just 24 hours earlier that I was thinking the exact opposite. Life didn't really look all that good to me then, no money of my own, no job, no girlfriend; it looked pretty damn bleak that was for sure. Then something amazing happened, not one, but two beautiful women deigned to teach me something amazing. They taught me self-worth, love and confidence. And the way they did it was wonderful ... Or perhaps that was just a coincidental lesson, because what I thought the whole time was, my mother is fucking my brains out and my sister is helping her do it... I was still resting on the couch with my eyes closed, my mother still astride my hips. I could feel her nails lightly scraping my chest, fingers trailing up and down slowly, stopping to circle a nipple every now and then. Mom was resting her head on my chest and slowly her breathing went back to normal as her fingers played across my chest. I opened my eyes and looked over at Holly as she sat next to us as she stroked our mother's back lightly, still smiling at us as we lay there. Mom eventually looked up at me and pouted her lips. "Hmm, you aren't worn out are you Bobby?" I looked down at that beautiful face and for a response gave a slight upward push of my hips and just smiled. My cock hadn't gone down yet; it was still just as hard as when we had started 15 minutes ago and still inside my mother. Mom just laughed softly and looked over at Holly "Looks like we still got life in him Holly, what should we do next?" Holly still smiling slowly got up and moved around and knelt down behind our mother and the next thing I knew I felt her mouth on the underside of my cock licking and slurping. At first I thought she was just trying to get us going again but next I felt Mom raising herself slightly and then more as she rose up off my cock. Cupping her pussy so as not to make a mess on the couch she got off me and moved over on her hands and knees next to me as Holly suddenly engulfed my cock and sucked it hard trying with little success to get what remained of my cum into her mouth. She used her hands and fingers to try to milk the very last drop out, but I could tell there was hardly any left. Mom meanwhile had sat down on the very edge of the couch and had cupped her pussy to keep all of my cum in. She then mentioned that she was going to clean up and for Holly not to make her brother have a heart attack while she was gone. Holly hearing this suddenly left my cock standing in the cool air and had quickly grabbed Mom's thighs to keep her from moving. Mom looked at on in confusion while Holly moved between her legs, where she looked at our mother and smiled a wicked grin. "Holly what are you doing ... Ahh, oh baby, oh god that's so good!" As soon as Mom started speaking Holly dove in and literally started sucking as hard as she could on Mom's freshly fucked pussy. And she was really going at it, trying to get as much of my cum out of her as she could. I had just cum myself about 5 minutes ago, but seeing that my cock was getting even harder, so hard in fact that it was almost painful, I started to slowly stroke it while watching Holly give our mother one hell of a ride. After less than a minute Mom started cumming, it couldn't have been anything else, she started thrashing from side to side and wailing. Even to my untrained eye I could tell she was having one hell of an orgasm. I just sat there and started stroking my cock, enjoying the show, my eyes drinking in everything. The small oval Holly made with her mouth, the little hood being pushed up on Mom's clit when Holly's tongue went up and down, the way Mom pinched and pulled on her nipples, the way her face scrunched up as she came, what a sight! Soon though, it was over, Mom came down from her orgasm and Holly sensed it as well and stopped sucking on her cunt. She resorted to lightly grazing the outside with her tongue a few more times until finally our mother pushed her away, totally and completely satisfied. Holly sat back on her heels and just looked at us. "So what's missing from this picture?" Sitting there stroking my cock and looking at her I decided to be a bit flippant. "Grandma?" Holly and Mom both looked at me with shocked looks on their faces then when I grinned they realized I was kidding and they burst out laughing. After the laughter had faded Holly looked at me and Mom again expectantly and that's when Mom got up and said we should all go get in bed. Oh well I thought, it was a fun night I guess, but it had to end sometime. Sighing I took my hand off my cock and started gathering my clothes. Holly did the same grabbing her shirt and shorts from the floor. With her robe and panties hanging over her arm Mom walked up the stairs to her bedroom and I heard her open the door. With our clothes in hand me and Holly both marched up the stairs with disappointment on our faces with the night being over with and started to split up to go to our respective bedrooms when Mom's voice stopped us. "Just where do you think you two are going?" I stopped and looked over at Holly; she was as surprised as me. What was Mom talking about? "Didn't you say it was time for bed Mom?" I asked, Holly murmuring the same question. Mom laughed then, chuckling she said "I said it was time for us to go get in bed, I didn't say anything about sleeping though, that is unless you guys are tired?" At that my face lit up and Holly's did as well as she squealed suddenly and ran over to Mom and kissed her right on the lips and in a split second had her tongue going halfway down Mom's throat. Mom just took it as it came and kissed her back just as fiercely. On the way upstairs thinking the fun and games had been over my cock had started to wilt a bit but now had come back to full strength, bloated and ready for more. I quickly made my way over to Mom's bedroom door just as she and Holly where making their way inside still lip-locked and running their hands all over each other. Somehow they made their way to Mom's bed and fell on it still locked together each moaning as hands found their targets'. I went around to the other side of the bed and sat down unsure of where and if I should join in. Because at the moment they were in a world of their own. And I don't know about most guys but seeing two very beautiful women going at it was one hell of a turn on for me, so I was more than content to just sit there and watch for the time being, giving my cock a stroke or two while watching. Holly rolled our mother onto her back in the middle of the bed and came up for air. When she raised up she immediately attacked Mom's nipples again and started pinching and pulling on them as she started to make her way down the front of Mom's body to her pussy. But Mom wasn't having it this time apparently; she stopped Holly before she made contact with her bottom lips. "Holly it's your turn now baby." She said smiling. Holly squealed and jumped onto the bed and then lay on her back and looked at us expectantly. Mom got up and grabbed her ankles and slid her over till she had her ass on the edge of the bed and told me to come over to her. I got up and came around to where Mom was holding her legs open. She then told me to hold her legs up for her, then Mom got down on her knees and slowly started stroking the inside of Holly's thighs and teasing the hell out of her. Mom got her tongue almost to the lips of Holly's cunt and Holly moaned in protest at the torment Mom was inflicting on her. "Holly you know Momma's gonna take care of you don't you baby?" Mom said as she continued to tease my sister. Holly nodded her head yes. "You felt left out when I said it was bedtime didn't you baby? You were afraid we weren't gonna take care of you tonight weren't you honey?" Holly was moaning continuously now at her mother's light touches and soft caresses. Slightly humping her hips upward to her mother's mouth begging for release. I couldn't help but stand there and watch this incredibly erotic sight that greeted me, Mom's tongue lightly tracing the outside lips of Holly's pussy, her hands doing a feather-light stroking holly's thighs. "Don't worry baby, Momma and Bobby are gonna take good care of you now honey, were gonna make you feel soooo good baby." She said continuing to tease her. I watched and could almost feel Holly's need, watching our mother torment her ever so slowly with her soft touches and soft words. Mom was now running her left hand palm down over Holly's pussy lips gently rubbing up and down, not quite touching her clit while her right hand was slowly passing out of sight down the crack of Holly's ass, moving slowly back and forth out of sight. Holly was writhing on the bed now, moaning and begging Mom to go down on her, to rub her clit, anything, she was begging hard now. Then I noticed Mom softly exhaling on Holly's lips and softly blowing air on her, and then all at once her hands stopped and she dove right into Holly's pussy, tongue diving deep into Holly's folds and her right hand doing something below her to Holly's ass, while here left was angled so she could rub Holly's clit in circles. Holly shrieked like a banshee caught in a whirlwind. I mean it was loud; Mom's earlier cries had nothing on Holly. At first I was a little alarmed, she started bucking and kicking her legs so hard that I almost let go, until I saw Holly's hands shoot to her nipples where they started pulling and twisting so hard I swear she was trying to bruise herself. Mom never letting up, sucking and tongue fucking her pussy so fast and expertly that she had Holly constantly moaning. And her moans and wails only got louder, until all at once they reached a crescendo and her whole body started shaking and her legs went stiff in my hands and all at once she went limp. Mom was sitting back on her heels and wiping her mouth and licking her fingers, I looked down at Holly a little concerned. Mom noticed the look and got out from between us and climbed up on the bed to look at Holly. She was still breathing hard but eyes were shut and she the slightest of smiles on her face. Mom reached down and pinched Holly's nipple but Holly just lay there. Mom turned around and sat down facing me and told me to lay Holly out on the bed so she could rest better. I did as I was told and made sure Holly was comfortable and then asked Mom if she was ok. "Of course she is, she just passed out is all, she'll wake up in a minute after she gets over it." She said smiling and gently caressing Holly's face. I sat down next to Holly's feet and just chatted with Mom for a few minutes while waiting for Holly to wake up. It didn't take her long before she started coming around, moaning softly at first then finally opening her eyes looking up at her mother as Mom gently stroked her face. "Thank you Mom" she whispered. "My pleasure sweetie" Mom said smiling down at her daughter, her fingers straying down the curves of her throat and back up to her cheek. I just sat there and watched the two most wonderful women I know stare at each other lovingly. Admittedly we all had had numerous orgasms, but I just couldn't help it, my cock was still hard as steel and I wanted more. But I just didn't have the heart to break the spell Mom and Holly were under, it was just beautiful they way they looked. Then Holly spoke "Mom, tell me something" "What do you want to know sweetie?" "Where did you learn how to do that? Making me, a woman, cum like that I mean" Holly asked. "Ahhh, you think your prudish old mother would know how to please a woman you mean" she said laughing softly. "Mom you aren't prude and you aren't old, I just mean that was the most fantastic orgasm I have ever had in my life." Holly said laughing. "I'll tell you another time sweetie, I promise." Mom said, then looked over at me and back to Holly. "And I'm glad you enjoyed it sweetie, but I'm sure your brother can give you one just as good, if not better" she said smiling mischievously. Holly grinned back at Mom then looked down at me and me sitting there holding my cock, still waiting for attention, just smiling and being patient. Holly then got up on one elbow to face Mom and me. "Mom, do you think you could go down on me again while Bobby does you from behind? All the time I was laying there first as much as I loved it I would have loved it even more if I had seen Bobby fucking you while you were eating me. Feeling him pushing your mouth into my pussy." She said grinning. "You have such a dirty mind baby, but I love you even more now." Mom said as she leaned down to tongue wrestle with Holly. Mom's left hand strayed down Holly's stomach until it reached her clit then she started applying pressure with her thumb and forefinger. I heard Holly gasp into our mother's mouth as she was being pleasured. Mom released her lip-lock on Holly and turned to me, her hand still gently squeezing Holly's clit. "Well stud, are you ready or should we give you another show to make sure that cock is nice and hard?" The way Mom said it and the way she looked, hair frazzled and spiky from all the activities tonight, something almost primal came out in me. I wanted to get off, and just watching Mom and Holly go at it had literally had me on edge the entire time. I got up and not even thinking clearly, my brain was so fogged over with lust it was as if I was on auto-pilot, I gently picked Mom up around the waist from behind and still holding her up in the air gently started to lower her onto my cock. Holly had grabbed hold of my cock and positioned it so it would go right in. As it sank in Mom groaned, she had her knees bent a bit and I lowered her head and upper body towards the bed. Holly got the hint and slid around till her ass was once again parked on the edge of the bed and her pussy was right in front of Mom's descending mouth. Still on auto-pilot I set Mom down on the floor on her knees while she attacked my sister's pussy. I watched for a moment, Mom sucking and rubbing Holly's clit while her daughter ran her fingers through our mother's short brunette locks. I just enjoyed the show and the heat and pressure Mom's pussy was giving me, I had come home again and this time I was gonna enjoy every absolute second of it. I started slow, just enjoying the hell out of those soft hot walls that gave me life so long ago. Coming back, giving my mother one inch at a time, feeling the heat she was giving me in return, that oh so good heat, it was heaven. I gripped her hips and started pumping in slightly faster, but not so fast to not enjoy every minute of it. This was right, this was where I was supposed to be, right here, right now. Mom was now starting to moan as I picked up the pace, her pussy on fire giving off even more heat as she was continuously sucking on Holly's clit, driving her wild. Her head bumping into Holly's cunt even more as I continued to pound into her, going faster now. Only 10 minutes had passed since I had started pounding into my mother, but it seemed like forever since I first entered her. I went even faster now, the mating dance I had surrendered to wanted release, the primitive desire to shoot my sperm into this woman's womb, my mother's womb, was getting uncontrollable. Holly was starting to cum, I could tell now, having seen her and Mom have similar orgasms. Just a day ago I wouldn't have been able to tell you what a female orgasm was much less describe it as it happened, but now, I could tell, Holly was in heaven. Starting to moan and writhe about, Mom's mouth never once leaving her pussy, with each of my thrusts into Mom her head would bump Holly's pussy causing her to moan. I was getting close, very close, I just couldn't help it, I was to the point where I was starting to get light headed. Holly's moans, along with my mothers were driving me crazy. Holly coming down from her orgasm looked me straight in the eyes and gave me a look I can only describe as lust incarnate. I started pounding as hard as I could and both Holly and Mom started wailing as a result and I knew they were cumming, I had to, I simply had to cum soon. It built and it built and I couldn't hold it anymore. I drove in deep and blasted the first shot and pulled back and drove back in so hard it shoved Mom's face up onto Holly's stomach, she started shrieking as I shot off into her. Driving as deep as I could I held still as the last few shots went as deep as I could manage into my mother, her still thrashing and wailing as I deposited the last of my seed into her womb. Her body going limp in my arms and laying her head on Holly's stomach, both breathing hard as if they had just ran a marathon. I saw two beautiful females laying there, me still connected to the one on her knees in front of me, I pulled back a little to ease my cock out of her, just a bit. And then, just as Mom looked back at me with a satisfied smile on her face, I smiled back, and then, still smiling, I felt myself falling and everything went black ... *** Slowly, as if coming out of a long sleep, my mind starting working, I could hear. I heard my mom and my sister talking. "Are you sure he's alright mom?" I heard Holly say. "Yes sweetie he's fine, he just passed out is all, it's a wonderful orgasm, women frequently pass out much the same as you did. But I have to admit I've never heard of a man passing out before." I heard Mom say. Slowly I opened my eyes and looked up at Mom and Holly looking down on me. I was on the floor, having passed out there. Holly with her red hair slightly covering her nipples with a concerned look and Mom just smiling at me, her hair still frazzled looking. I couldn't help but smile, I felt like the world was giving me a beautiful day and I never wanted it to end. Mom felt my head and checked my pulse, why I have no idea, I think it was more to pacify Holly than anything else. I slowly sat up and on impulse kissed my mother, our tongues went into each other's mouths immediately. Not with the tongue wrangling passion we had shared earlier, but more with a sense of love and tenderness. Tasting my sister on her tongue caused me to love them both even more, sharing this, this night, this wonderful night. When I pulled back Mom was all smiles and I looked over to my sister, she was looking back at me expectantly. I smiled a small smile and kissed her much the same as I had mom, only she was a little more aggressive than Mom was, biting my lower lip slightly. When I pulled back she still had her eyes closed and was smacking her lips like she had just ate something tasty, then I realized she could taste herself on my tongue from when Mom kissed me. When she opened her eyes she grinned at me. "I taste yummy." She said, moving her tongue over her lips as if getting every taste she could off her lips. Mom laughed at her daughter's antics, and suddenly looked thoughtful. "You know sweetie, your brother hasn't taken care of you yet." Holly looked at Mom and got a considering look on her face. "Hmmm, your right Mom, he hasn't, now isn't that just rude of him?" She said in a teasing tone. "Yes it is sweetie, very rude in fact." Mom said looking at me sternly. I could tell they were just kidding but I decided to play along anyway. "Your right Mom, Holly I am so sorry for not taking care of you earlier. If you will forgive me, I will service your pussy for you promptly." I said with a half-bow while sitting there. Holly and Mom both burst out laughing and after a few seconds I did as well. After our mirth faded Mom said she wanted something to drink and asked us if we wanted anything. At that moment I realized I was thirsty as hell and Holly was the same, so Mom went to the kitchen to get us some bottles of water. Virginity Has Its Perks Ch. 02 When she got back me and Holly were sitting on the edge of the bed still naked and had started chatting about school and college life as if this was all natural. Me, my mother and my sister naked and talking about normal things. After a few minutes and 3 empty bottles later I looked over at Mom who was rubbing one of her nipples unconsciously while chatting to us. "I think someone is ready again." Looking suggestively at Mom. Mom just laughed. "Honey I'm always ready." And she lay back and spread her legs and looked at me, just waiting with a little smile on her face. I started to climb further up onto the bed and get into position to taste my first pussy ever when I felt Holly's hand on my arm. "Hold on little brother, my pussy is next, Mom can have more later." She then looked at Mom and stuck her tongue at her. "Oh you brat." Mom said hitting Holly with a pillow and laughing. "Get up on your knees Mom and face the headboard." Holly ordered. Mom knowing what was in store moved into position. Holly then lay back and slid under our mother and I saw her throat working, she starting to lap at Mom's pussy. I watched for a minute then Holly stopped, she slid out a little and raised her head to look at me. "And just what are you waiting for Bobby? Get down there and eat my pussy like a good brother." She then stuck her tongue out at me then moved back and resumed her ministrations on our mother. Mom looked back over her shoulder at me then. "Do as your sister tells you Bobby." She then winked at me and closed her eyes and started rolling her head as if doing neck exercises, Holly obviously giving her pleasure from below. Well I thought to myself, two women both telling me to do the same thing, who was I to argue? I climbed up and got between Holly's legs and lowered my head till my nose was just above Holly's cunt lips. Then I remembered what Mom had done earlier and slowly started to tease the hell out of Holly. Lightly running my hands up her thighs I started exhaling on her lips, slowly pursing my lips to focus the air on her clit. Ever so slightly teasing the little hood above her box with my tongue, just barely wetting it humming softly. I could tell she was starting to get turned on and at first I thought she was about to slide back and chew my ass out for the teasing. But the minute she stopped her tongue my Mom reached down and grabbed a handful of hair to keep her in place. She then went back to pleasing our Mother, and I kept up my light caresses. After just a minute or so of this her legs were starting to shake and her was pussy practically dripping. I decided she had had enough and was ready. I remembered what Mom had done, dove straight in tongue first, I decided to do something a little different. I raised my head back a bit and slowly and lightly lowered it down till my lips touched her clit, then I raised the hood and gently started sucking the clit. I knew I was doing something right because I heard her muffled moans coming from underneath our mother. Her legs tried to wrap around my head but I had my forearms in place holding them back. I had to wrestle with her legs for a few minutes as I kept up my sucking of her clit, it was really starting to drive her wild. As her moans picked up our Mother started cumming, I guess all the moaning Holly was doing was really getting Mom going, she started making these little 'Oh' sounds. With Mom cumming and Holly getting close my cock started to rise, it must be the female voice, just the sounds of them both getting off had me revived to full strength in no time. I had to straighten it a bit as it was starting to poke into the mattress painfully. Holly was really getting close now as her moans got louder, and as a result Mom was starting to buck her hips as her orgasm hit her full force, throwing her head back and wailing as Holly expertly assaulted her pussy. Seeing this I doubled my efforts to bring Holly off, I was no expert but just by watching my mother and my sister do each other I applied what I had learned and started tonguing Holly's pussy as hard and as deep as I could go with it. That did the trick, she started humping my face as hard as she could, almost throwing her hips into the air. I just kept up my ministrations until her orgasm subsided and she stopped moving. Mom was slowly moving off Holly to the side of her, sitting on one of the pillows with a dreamy look on her face and a smile on her lips. I gave Holly one last lick with my tongue that made her shudder then moved over to the edge of the bed and sat facing them, slowly stroking my cock. I didn't just jump right on Holly, not because I didn't want to, but I know they are in their cooling down glowing stages, and I decided to let her enjoy that. Mom looked over at me and grinned. "I don't know what you did to her Bobby but that was fucking awesome!" Mom said giggling like a school girl. Holly sat up and slid back till her back was to the headboard and looked at Mom. "You never had a hummer before Mom?" Holly asked. "Is that what it was?" Mom said, surprised. Holly laughed then. "Of course it was, didn't you know that?" "Hmmm, well I've had people do something similar before but never like that, that was just amazing, thank you sweetie." Mom then leaned down and kissed Holly gently, thanking her in as sweetly a way as possible. They kissed for a moment then Mom broke the kiss and looked over at me slowly stroking my cock. "Looks like someone wants more..." She said suggestively looking at me and then looking at Holly. Holly looked at me and licked her lips like she was getting ready for a lollipop and started crawling towards me. "No honey, I think he wants something else ..." Mom said as she was running her hand over Holly's ass and up and down Holly's slit. At that Holly's look changed and with her hair hiding half her face I couldn't tell for sure but she almost looked scared. I stopped stroking my cock then and looked in Holly's eyes'. "Holly is something wrong?" I asked, noticing my mother slowly slipping a finger into Holly's pussy from behind. Mom not seeing the look on Holly's face kept moving her hands. Holly then started to speak but I heard a gasp from Mom. "Holly you're a virgin!?!?" Mom said shocked To be continued... Virginity Has Its Perks Ch. 03 This is a work of fiction. (Sorry for the wait guys and gals, had to go out of town for work and just recently been able to get some free time for writing, thanks again for all the e-mails and comments, they do mean a lot and I really do appreciate them, read on and enjoy!) * Tonight was a good night I thought lying in bed. I had lost my virginity this afternoon and had developed a special relationship with my mother and my sister. One I hoped would last for the rest of my life. Earlier in mom's bedroom I had found out that Holly, my older sister, the popular girl from school, the one that dated good-looking guys regularly, was in fact a virgin as well. To be honest I could have gone all night, but when Mom had discovered that about Holly and had, perhaps unthinkingly, blurted it out it made Holly break down into tears. When that had happened Mom just gathered her close and held her as she cried, she had motioned to me silently to leave and go get to my own bed. I guess she wanted to talk to her; I couldn't help but feel a little guilty as I had left the room, mainly because I felt so damn good. But nevertheless guilt was still there; I was happy and my sister was crying, just didn't feel right. When I had got back to my room my cock had wilted and tonight's events had slowly started to catch up with me and I took a shower in the bathroom I shared with Holly in between our respective bedrooms. After showering I put on a pair of boxer-briefs and lay down to try to get some sleep. So here I lay, waiting for sleep to come, even though I knew it would be awhile, replaying all the events of the past 12 hours over and over in my head. Strangely enough even after all the wonderful lustful sex I had had my cock still had life, just thinking of what we had done earlier had caused my cock to stir and stretch out my shorts, tenting up against the fabric. After a few minutes of staying hard and knowing I wouldn't get any sleep if I didn't relieve the pressure I finally said fuck it and removed my shorts and slowly started stroking it. Closing my eyes I started drifting into my memories of tonight, with a smile on my face I continued stroking. "Just what do you think you are doing?" I heard my mother ask. I opened my eyes to see her standing there just as naked as I was looking at me with a small smile on her face. "Well, um, I was just taking care of myself Mom." Still stroking I wondered why she was in here instead of with my sister, and said as much. "Well I've been talking with your sister and she wants you to take her virginity, tonight." Saying this she sat down on the edge of the bed and took over stroking my cock, pushing my hand away. "So son of mine, think you are up to it?" She asked smiling, continuing to stroke me. "Of course I am, can't you feel it?" I asked laughing. Mom laughed then too and got up told me to follow her. I got up and followed mom from the room, my eyes locked on that beautiful ass as it sauntered through the doorway and into the hall. When we entered Mom's room Holly was sitting there on the bed with her head down, she looked up as we entered. Her eyes were still a little puffy and looked like she had been crying but she smiled at us as we entered and came over to me and put her arms around my neck and snuggled her head into my shoulder. I just held her for a minute while Mom walked over to the bed and sat on the edge. "I'm sorry Bobby; I hope I haven't ruined our night." Holly mumbled, still hugging me. "No sis you haven't, we were only worried about you, not ourselves." Slowly I started stroking her hair, running my hand from the top of her head down to the base of her neck, comforting her. After a minute of this Holly pulled back and looked into my eyes and said. "Bobby, will you make me a woman tonight?" I smiled and replied "Of course." Hearing that Holly grinned and took my hand and led me over to the edge of the bed. Letting go she crawled up on the bed and still on her hands and knees looked over at her shoulder at me and winked. "Mom, do you think you can get me ready for Bobby?" She asked, looking over at our mother. "Of course sweetie, I'll make sure you are good and wet for him." Mom replied standing and walking over in front of me and crawling onto the bed behind Holly. Holly still on her knees shook her ass playfully at her mother as her mother's lips closed over her pussy and gently started nibbling and tonguing her pussy lips. Holly looked back at me again and gave me a 'what are you doing stare?' Unconsciously I had begun to stroke my cock as my mother had started the fine art of cunnilingus on my sister, making it next to impossible not to become aroused at the sight. Holly then kind of glanced over at our mother and back me again quickly and I got the idea. Moving closer to Mom I asked "Mom, do you mind if I warm up a bit for Holly?" Our mother knew exactly what I meant, she had been kind of half-laying on her side twisting up to eat Holly but now she moved onto her knees and spread her legs slightly in answer to my question. Seeing the invitation I moved in behind Mom and rubbed my cock up and down her labia and found her to be slightly dry. Using a little bit of spit I polished the head of cock with it and started rubbing it up and down through Mom's outer pussy to see if I could get her juices flowing. Apparently I was doing a good job, after a minute she had started to leak noticeably, either that or the fact she was eating her daughter out and getting ready to fuck her son again was turning her on. With Mom good and wet now I gave the head of my cock one last rub through her folds and then slowly pushed in causing Mom to moan as I entered. With this just being a warm up I knew I didn't want to cum in Mom, not this time, I was saving that for Holly, so I took my time, long and slow strokes in and out of her pussy. Looking down, seeing Mom's pussy lips slowly coming slightly out with me when my cock withdrew was such a turn on, it was taking every ounce of my self control not to turn into a rutting beast and ravage this wiling female below me. "Alright Bobby." Mom said suddenly, breaking the spell I was under, I had become almost hypnotized watching my cock slide in and out of my mother. I glanced up and saw Holly looking back at me grinning and Mom looking over her shoulder at me doing the same. I just smiled and gave Mom one last quick thrust that made her jump a bit and slowly withdrew. As the last inch came out and the head of my cock popped out into the open I couldn't help but give a sigh of regret. Mom's heat and pressure where something I never wanted to be without, but I knew I wouldn't be left hanging for long. As soon as I pulled all the way out Mom moved over on the bed and made room for me as I climbed up and got close to my sister's very wet and very excited looking pussy. "Ok Bobby, Holly is ready for you, but listen to what I say, do not go slow, it's better to have quick pain than letting the pain build by slowly doing it, understand?" Mom asked me looking at me seriously. I nodded in understanding looking at my sister who had her head down and her hands gripping the sheets in front of her like she was going to strangle them. Mom then reached over and placed my cock at my sister's opening and let go. I looked down, and suddenly I didn't want to do it, I just knew it was gonna hurt my sister and I didn't want to cause her any pain. Looking over at Mom she seemed to understand what was going through my head. "Bobby, this is natural, women go through this, and its better this way than in the back seat of a car or in a cheap motel with some loser that says he loves you just so he came take your cherry and cum ten seconds later. Trust your mother in this Bobby." She said, rubbing my back, lightly scraping it with her nails. "Bobby, listen to Mom, I know it will hurt, but I also know you really do love me, so please, help me ..." Holly said, still not looking back. Still a little unsure about it I just decided to trust the resident female expert on vaginal penetration, our Mom, and slowly started to inch inside my sister's tight sheath. And man was she tight, Mom was tight as well but not like this, this was like a too small pair of gloves for my hands. I made progress, but slow, slowly I could feel her vaginal walls stretching to accommodate me, I knew I could go in harder but the less pain I caused Holly the better. Almost as soon as I started pushing in Holly started moaning, feeling a man entering her for the first time, feeling herself stretch. I pushed in a little farther, never pulling back and finally after what seemed like hours but in fact only mere moments I reached her hymen. At that point I pulled back until I was almost out and moved back in, intending to make sure her passage was good and lubricated so nothing would impede my progress. Mom had gotten up and was standing on her knees behind me on the bed; she was reaching around me now, lightly scraping my chest and twisting my nipples occasionally. Mom was driving me crazy with her caresses; self-control was a motherfucker when someone was doing that to you. I couldn't seem to concentrate fully on what I was doing, still going slow, but now I was starting not to care if Holly was loose enough now. It was as if my brain was shutting off with a little voice in the back of my head telling me what to do, do it, do it, do it, it chanted, on and on. In the haze of shrouded lust I rolled my head back and shut my eyes just as I was going back into Holly when I suddenly felt Mom reached around in front of me and suddenly slammed her hips on mine and my cock shot straight up into Holly. I came back to my senses almost immediately as Holly moaned in pain and I felt cock power through her Hymen almost effortlessly. I tried to pull back but Mom locked us in place with her hands on Holly's hips and said "Don't move, she will feel better if you just hold it in till some of the pain eases." Nodding my head that I understood Mom moved from behind me and then got her head right under Holly's pussy and slowly started licking. I was concerned about Holly; she hadn't said a word since that one moan when Mom pushed my cock through her cherry. Still holding myself inside her I rubbed her back with my left hand, hoping she would feel better. Less than 30 seconds had passed since Holly was de-virginized and she hadn't made a sound, but now I felt a little movement from her. Looking down I could see our mother still working on Holly's pussy, her tongue peeking between my cock and her pussy occasionally. Then a small moan came from Holly, low at first then it picked up and she started to move. Slowly at first, she leaned forward moving her pussy off my cock a half inch at a time and back. Little by little she was starting to work herself up to a rhythm. I just held still, not wanting to hurt her or cause her pain I just kept my cock in place, not moving with her, just kneeling on the bed. The feeling of her tight pussy was driving me crazy, but this time I didn't lose my mind, I simply put my love for Holly at the forefront and my lust on the back burner, when Holly was ready she would let me know. Mom was moving her ass around so Holly and she would be in a sixty-nine, almost as soon as Mom placed her pussy before Holly she dove in. With them both licking and nibbling I started to wonder if Holly was ok, she certainly didn't seem to be in pain at the moment and I started wondering what to do. "Holly, are you ok now?" I asked feeling her thrusting on me now a little harder and a little deeper. "Yea Bobby it doesn't hurt nearly as much now, but go slow at first ok, you can go deep, but just go slow." She said, resuming her ministrations to our mother. Finally getting the green light I matched her rhythm and started to push in deep, at that Holly moaned and I stopped, afraid that I had hurt her. Feeling me stopping Holly growled angrily and slammed her hips backward and I got the point. I pushed back in and once again Holly started moaning, and this time I knew it wasn't pain. Bottoming out I slowly pulled back out and pushed back in till I was balls deep once again. Holly was continuously moaning now and I was hoping it was both what I was doing and what Mom was doing below. After a couple of minutes of this I decided to chance going faster, after all I reasoned that Holly could always tell me to slow down. Besides, her pussy was so tight and wet that it was driving me crazy going so slow like this. I picked up the pace, not from slow to fast, but rather from slow to only a little faster and Holly didn't seem to mind, she thrust back on me just as hard, her hips slamming into me as we fucked. Mom was crawling out from under Holly now and her chin was slightly red from Holly's blood, but apparently she didn't mind. She wiped her mouth with her hand and got off the bed and stood there smiling at us, fucking our brains out. "Bobby why don't you hold still and let Holly just fuck back onto your cock instead of thrusting, that way she can control the pace and slow down if it hurts?" She said moving behind me, her hands now on my hips rubbing and caressing my stomach. "Sure Mom, all yours Holly." I said holding myself still while Holly started thrusting back onto my cock with a little more vigor. "Bobby spread your legs slightly and hold her hips, you have to make she doesn't pull you all the way out when she goes forward." Mom said still lightly caressing my abs and chest. Always listen to your mother I thought as I spread my legs and lightly gripped Holly's hips as she continued to fuck me, seeming to get faster by the minute. Mom was now running her hands along my back and the crack of my ass, lightly rubbing my opening down there, nails scraping my back, basically she was driving me crazy with all this. Mom never fails to amaze me, an experienced woman always knows what to do, that's the lesson I learned tonight, and I love her to death for it. Holly's hips where now a blur and she was moaning like crazy now, I just knew she was going to cum soon, but I still had awhile to go, having already cum more than once tonight. Mom whispered in my ear "Cum with your sister Bobby, cum in her, let her feel a man's sperm for the first time in her pussy, let yourself go ..." Hearing Mom's sexy-ass voice was unbelievable but still I couldn't feel the pressure build yet. "Um, Mom I can't really cum yet, I just don't feel it right now" I whispered back. "Don't worry baby, Momma will help you cum." Mom whispered and then reached down to where Holly's hips and my cock were connected and held her hand there for a moment, two of her fingers playing with my balls smearing the coating of pussy juice that had collected there. What was she doing? I thought. Playing with my balls felt great but it wasn't gonna make me cum, although I didn't want to tell her that. But once again Mom surprised me. After playing with my balls for a moment she moved behind me and started rubbing my back again, I could also hear her doing something with her mouth. Then I felt her hand once again rubbing my asshole, and then amazingly I felt her tongue on me down there. And that was a big turn on, her soft warm wet tongue making little probes on my opening, soft little stabs that were driving me crazy. Just at that moment Holly started slamming into me hard and moaning like crazy, that was it, she was cumming and I was a little disappointed, I wasn't cumming with her. Then I felt Mom probe me harder this time, only this time it wasn't her tongue, it was her fingers. Suddenly I felt two fingers shoot up my little hole and an immense pressure built almost instantly and suddenly I was experiencing one of the most intense orgasms of my life, it was unbelievable. It felt like I was draining the very life out of my body and into Holly, shot after shot of sperm went racing up and out of my cock and into Holly at what seemed like the speed of light, it was incredible. Mom was now moving her fingers and pushing inside me and I almost doubled over as it hit me again with pleasure and I shot even more into Holly, spurt after spurt going deep into Holly's womb. Holly for her part had stopped and was shaking as her orgasm had hit her and she felt my shots go deep into her body, her moaning had stopped now and she was just arching her back and shivering with carnal delight. And finally it was over, Mom withdrew her fingers and patted me on the back and left to go to the bathroom to wash herself off. With my cock completely and utterly drained and starting to wilt I collapsed to the side of Holly as she was resting her head on her forearms with her eyes closed slowing her breathing back down. I just lay there on my back and looked up at the ceiling, breathing hard and once again was in complete amazement at what tonight had brought. Mom finished washing up in the bathroom had walked back and was looking at us with what could only be called a considering look. Holly finally got up into a sitting position and looked down on me and smiled and said "Thank you Bobby, you were wonderful" Then she kissed me softly, not as a sister would kiss her brother, but as a lover, soft and with tenderness. Holly broke the kiss first and looked up at Mom who was smiling at us now and went over to her and kissed her as well. After a moment she broke the kiss and said "Thank you too Mom, you and Bobby both made me feel like I was the only woman in the world tonight and it was wonderful." Mom gathered her in her arms and hugged her. After a minute Mom said "Come 'on baby, let's get you into a nice bath and get you cleaned up, you still have a bit of blood on you down there." "Mom I don't know about you and Bobby but if I climb into a nice warm bath I'm gonna fall asleep in it and not wake up for a week." Holly said laughing tiredly. Mom and I both laughed along with her and we all agreed that for tonight it was bedtime. I got up and all of us went into Mom's big bathroom and each got a washcloth and scrubbed down a bit, too tired even for a shower. After washing up and getting as clean as we could we all started out to our beds. Almost to the door Mom asked "You guys don't want to sleep with your mother?" Holly and I looked at each other and realized Mom was serious, we just each thought that Moms bed was for fun and games, we didn't realize we would actually all share it. Mom had turned the comforter down and climbed in and beckoned us over. Telling me to shut off the lights first Holly climbed in on one side and after I had hit the lights I climbed into the other. Snuggling up to my mother I felt warm and loved, just like when I was a kid, and Holly had the same idea, she was snuggling in just like I was, our hands meeting and locking together over our mothers stomach. Mom's hand was caressing my hair now, and my eyes becoming adjusted to the dark I could see her other hand on holly's head as well, softly stroking her hair. Then I don't know why, maybe it was impulse, instinct, who knows why. Mom's right breast was near my head and I just naturally took her nipple into my mouth and started sucking softly. I glanced over at Holly as she took the other breast, nipple slipping between her lips, suckling gently. Mom sighed softly and contentedly and cooed to us both happily as we nursed on her breasts, wishing there was milk in them. Wondering what tomorrow would bring, I suckled until I fell asleep.